Eric BellOof, I started drafting this post over a year ago. So much for maintaining a cadence.
It feels like I’ve spent most of my life trying to keep track of stuff I want or need to do. From paper notes to digital lists to online syncing, from ephemeral to Sisyphean to obsessive to mindful, it’s been a journey.
Finding a system
To-do lists were always a lot of stuff. Writing down things to do, adding to the list, updating the list, reorganizing the list, losing the list, recreating the list. Keeping track of literal or metaphorical piles of notes and notions, in planners or folders or binders or boards. Easy to get lost in, tedious to maintain.
My personal epiphany came when I was gifted a copy of Getting Things Done, by David Allen, after a particularly quirky but unsuccessful job interview in my temping days before grad school. That book’s subtitle, “the art of stress-free productivity,” held for me the same seductive appeal as the Hitchhiker’s Guide to the Galaxy’s mythical DON’T PANIC.
The GTD method (with its own schools of acolytes) came with a few distinctly insightful strategies:
- Capture everything to reduce mental overhead. Getting outstanding tasks out of my head so that I stopped spending constant mental energy trying to keep track of it all. Instead, I could write each thing down in a standard Inbox-like place and then relax, knowing I could predictably find it later.
- Regular review cadence. At the end of a day or week, go through my inbox and file everything into an appropriate list. At the end of a week or month, go through each of my project areas to update or reprioritize or just remind myself what’s next to do.
- Contextual lists. When reviewing or filing to-dos, group them and my broader projects into “areas” of my life. These contexts could then serve as triggers for surfacing relevant projects. For example, “school” or “workplace” or “[specific hobby]”. This aspect of GTD was the most challenging for me, both as a student and as the world moved into digital tools. My tasks were rarely dependent on physical context, I had no set working hours, and I could work on most of my projects from anywhere with a laptop and internet.
- Other pieces of the approach, like clarifying tasks into small actionable steps, or triaging quick tasks from bigger chunks of focus time, were less revolutionary to me at the time but nonetheless valuable.
The GTD approach provided a pragmatic mental framework for capturing, organizing, and maintaining a flexible large task list across various areas of my life and projects.
Finding the right tool
Having a method is great, but where to actually put everything? From paper notebooks and bullet journals to a parade of software and apps, I spent years iterating through tools trying to find the right balance of structure and flexibility that works for me.
In high school it was paper planners, class handouts, and noticing that noets scrawled in red ink stayed legible on my hand longer than blue ink. In college it was a desktop of digital sticky notes, a binder for each semester, and a paper filing system. By grad school I had finally succumbed to my first cell phone and began switching from paper planners to digital calendars. Soon I could access notes and tasks from multiple devices, and eventually my phone was key.
Various tools and their tradeoffs for me:
- OmniFocus. Structured with GTD in mind, a little too easy to drown in just a few too many layers.
- Todoist. Web-based and better cross-platform access, but too few facets.
- Things. Simple and optimized for GTD, but at a time when I was trying out Android and Windows phones, being constrained to Apple devices (without even a web view) was too limiting.
- Asana. Excellent for cross-team visibility and a useful view for each user, easily the best updates email design I’ve encountered. Overkill for an individual.
- Trello. The right balance of constraints and flexibility, with solid cross-platform compatibility. Trello’s main downside has been a lack of cross-board views. While it’s added some useful automations and syncing over the years, it still lacks a reliable way to see a meta-view of the top items in specific lists across boards.
Ultimately, Trello is what I’ve come back to for most of my personal project areas. The lack of a cross-board view is an annoyance but also a useful constraint to force a little bit of focus.
Building habits one brick at a time
For such a long time I repeated a cycle. Getting frustrated with my current broken system, getting inspired to sketch out a new idea and approach, and then getting bogged down making it happen in one big bang rollout.
Eventually I learned more about habit formation, mostly by way of the personal-professional cross-polination that came from designing for it. Shoutout to Nir Eyal’s talk at a “healthy habits” hackathon back in the day. Reducing hurdles to the intended workflow, making the desired action clear and intuitive, and creating nudges to do the next thing.
The key to improving my habit-building was to add one small sustainable piece at a time and then iterate gradually, rather than try to plan out and execute a massive change in routines all at once. For example, the visual at the top describing how my various task lists relate to each other is the last thing I made, an after-the-fact keystone rather than a pre-laid-out master plan. In some ways, this has always struck me as a corollary to the apocryphal story of George Fox’s advice to William Penn to “carry the sword as long as you can” (to do it until you realize you can’t do it anymore), about letting change happen organically without trying to force it.
Done list
An insight along the way, done lists are the practice of making (or keeping) completed items visible. I was introduced to the concept while working at Viki, where we started using a daily done list feed as a way to share updates internally, as a replacement for standups. At first it felt helpful for cross-team visibility of everyone’s activity, but gradually it started to come across as a little forced and performative.
In my personal use I’ve found it surprisingly useful. For me, this practice means simply keeping a Done Trello list next to my Today list, instead of immediately archiving (and hiding) each task as it’s finished. It has proven to be an encouraging reminder of my own general productivity. When I feel like I can’t get anything done, glancing over at my Done list reminds me of all the things I’ve actually accomplished recently.
Reflections
A few coworkers over the years have commented that I’m the most organized person they know. And yet I still feel like an imposter who’s struggled most of my life to get a handle on everything I want or need to do. Not to mention living in a world of task management internet forums, or working alongside various levels of managers orchestrating entire teams worth of activity.
Getting here has been such as long slog of adding sustainable habits one brick at a time, with periodic “raze it to the ground!” moments. Making the above visualization of my current organization system felt like a milestone, and prompted this attempt to capture my journey.